OA11589A - Tricyclic sulfonamides and their derivatives as inhibitors of matrix metalloproteinases. - Google Patents

Tricyclic sulfonamides and their derivatives as inhibitors of matrix metalloproteinases. Download PDF

Info

Publication number: OA11589A
Authority: OA; OAPI
Prior art keywords: tetrahydro; sulfonylamino; dibenzofuran; acid; hydroxy
Prior art date: 1998-07-30

Application number

OA1200100027A

Other languages

English (en)

Inventor

Patrick Michael O'brien

Joseph Armand Picard

Drago Robert Sliskovic

Original Assignee

Warner Lambert Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-07-30

Filing date

1999-06-02

Publication date

2004-07-30

1999-06-02 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2004-07-30 Publication of OA11589A publication Critical patent/OA11589A/en

Links

102000002274 Matrix Metalloproteinases Human genes 0.000 title claims abstract description 30
108010000684 Matrix Metalloproteinases Proteins 0.000 title claims abstract description 30
239000003112 inhibitor Substances 0.000 title abstract description 17
229940124530 sulfonamide Drugs 0.000 title abstract description 5
150000003456 sulfonamides Chemical class 0.000 title description 2
-1 sulfonamide compounds Chemical class 0.000 claims abstract description 61
238000011282 treatment Methods 0.000 claims abstract description 34
238000000034 method Methods 0.000 claims abstract description 23
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 18
206010028980 Neoplasm Diseases 0.000 claims abstract description 15
230000004054 inflammatory process Effects 0.000 claims abstract description 13
206010061218 Inflammation Diseases 0.000 claims abstract description 12
201000011510 cancer Diseases 0.000 claims abstract description 12
208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 11
208000037260 Atherosclerotic Plaque Diseases 0.000 claims abstract description 10
206010019280 Heart failures Diseases 0.000 claims abstract description 10
102100030416 Stromelysin-1 Human genes 0.000 claims abstract description 9
206010003246 arthritis Diseases 0.000 claims abstract description 9
230000001684 chronic effect Effects 0.000 claims abstract description 9
208000030507 AIDS Diseases 0.000 claims abstract description 8
108010016160 Matrix Metalloproteinase 3 Proteins 0.000 claims abstract description 8
230000001154 acute effect Effects 0.000 claims abstract description 8
206010019196 Head injury Diseases 0.000 claims abstract description 7
208000024777 Prion disease Diseases 0.000 claims abstract description 7
208000006011 Stroke Diseases 0.000 claims abstract description 7
210000000265 leukocyte Anatomy 0.000 claims abstract description 7
208000037803 restenosis Diseases 0.000 claims abstract description 7
230000002861 ventricular Effects 0.000 claims abstract description 7
206010013801 Duchenne Muscular Dystrophy Diseases 0.000 claims abstract description 6
208000001132 Osteoporosis Diseases 0.000 claims abstract description 6
208000002193 Pain Diseases 0.000 claims abstract description 6
208000018737 Parkinson disease Diseases 0.000 claims abstract description 6
208000025865 Ulcer Diseases 0.000 claims abstract description 6
230000001363 autoimmune Effects 0.000 claims abstract description 6
230000009545 invasion Effects 0.000 claims abstract description 6
206010028417 myasthenia gravis Diseases 0.000 claims abstract description 6
230000036407 pain Effects 0.000 claims abstract description 6
208000028169 periodontal disease Diseases 0.000 claims abstract description 6
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
208000020431 spinal cord injury Diseases 0.000 claims abstract description 6
231100000397 ulcer Toxicity 0.000 claims abstract description 6
102100027995 Collagenase 3 Human genes 0.000 claims abstract description 5
230000010339 dilation Effects 0.000 claims abstract description 5
108010076503 Matrix Metalloproteinase 13 Proteins 0.000 claims abstract description 4
208000007474 aortic aneurysm Diseases 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 117
125000000217 alkyl group Chemical group 0.000 claims description 90
239000002253 acid Substances 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 29
150000001413 amino acids Chemical class 0.000 claims description 26
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 23
125000003545 alkoxy group Chemical group 0.000 claims description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 13
125000001072 heteroaryl group Chemical group 0.000 claims description 13
239000004305 biphenyl Substances 0.000 claims description 12
235000010290 biphenyl Nutrition 0.000 claims description 12
229940080818 propionamide Drugs 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000003884 phenylalkyl group Chemical group 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
230000005764 inhibitory process Effects 0.000 claims description 8
206010002027 Amyotrophy Diseases 0.000 claims description 7
206010059245 Angiopathy Diseases 0.000 claims description 7
208000034189 Sclerosis Diseases 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000004663 dialkyl amino group Chemical group 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 6
208000027418 Wounds and injury Diseases 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 5
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000004103 aminoalkyl group Chemical group 0.000 claims description 5
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
230000002757 inflammatory effect Effects 0.000 claims description 5
125000005041 acyloxyalkyl group Chemical group 0.000 claims description 4
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
KTOYYHAFUWMZLO-MRXNPFEDSA-N (2r)-3-methyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanoic acid Chemical compound C1CCCC2=C1C1=CC=C(S(=O)(=O)N[C@H](C(C)C)C(O)=O)C=C1O2 KTOYYHAFUWMZLO-MRXNPFEDSA-N 0.000 claims description 3
239000001384 succinic acid Substances 0.000 claims description 3
CXCVBZCJVAXMHS-LJQANCHMSA-N (2r)-2-phenyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)acetic acid Chemical compound C1([C@@H](NS(=O)(=O)C=2C=C3OC=4CCCCC=4C3=CC=2)C(=O)O)=CC=CC=C1 CXCVBZCJVAXMHS-LJQANCHMSA-N 0.000 claims description 2
MNTISXAWZZNIAP-HXUWFJFHSA-N (2r)-3-(1h-indol-3-yl)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)propanoic acid Chemical compound C1CCCC(OC2=C3)=C1C2=CC=C3S(=O)(=O)N[C@@H](C(=O)O)CC1=CNC2=CC=CC=C12 MNTISXAWZZNIAP-HXUWFJFHSA-N 0.000 claims description 2
HNEFGOMOYFKACW-LJQANCHMSA-N (2r)-4-(phenylsulfamoyl)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanoic acid Chemical compound C([C@H](C(=O)O)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CS(=O)(=O)NC1=CC=CC=C1 HNEFGOMOYFKACW-LJQANCHMSA-N 0.000 claims description 2
IDZXKDMOCMXAPR-HXUWFJFHSA-N (2r)-4-benzylsulfanyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanoic acid Chemical compound C([C@H](C(=O)O)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CSCC1=CC=CC=C1 IDZXKDMOCMXAPR-HXUWFJFHSA-N 0.000 claims description 2
WQTGBJAPYVORGF-HXUWFJFHSA-N (2r)-4-benzylsulfanyl-n-hydroxy-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanamide Chemical compound C([C@H](C(=O)NO)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CSCC1=CC=CC=C1 WQTGBJAPYVORGF-HXUWFJFHSA-N 0.000 claims description 2
WNYPNJGYOHRJDD-HXUWFJFHSA-N (2r)-4-benzylsulfonyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanoic acid Chemical compound C([C@H](C(=O)O)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CS(=O)(=O)CC1=CC=CC=C1 WNYPNJGYOHRJDD-HXUWFJFHSA-N 0.000 claims description 2
JQKACVYQFTUZRS-JOCHJYFZSA-N (2r)-4-phenyl-2-(6,7,8,9-tetrahydro-5h-fluoren-2-ylsulfonylamino)butanoic acid Chemical compound C([C@H](C(=O)O)NS(=O)(=O)C=1C=C2CC3=C(CCCC3)C2=CC=1)CC1=CC=CC=C1 JQKACVYQFTUZRS-JOCHJYFZSA-N 0.000 claims description 2
NAUKORUGXNMHQK-JOCHJYFZSA-N (2r)-5-(1h-indol-3-yl)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)pentanoic acid Chemical compound C1CCCC(OC2=C3)=C1C2=CC=C3S(=O)(=O)N[C@@H](C(=O)O)CCCC1=CNC2=CC=CC=C12 NAUKORUGXNMHQK-JOCHJYFZSA-N 0.000 claims description 2
RURBVYFVVRWLNK-HXUWFJFHSA-N (2r)-5-phenyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)pentanoic acid Chemical compound C([C@H](C(=O)O)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CCC1=CC=CC=C1 RURBVYFVVRWLNK-HXUWFJFHSA-N 0.000 claims description 2
MLBBPXVRDNIHJC-OAQYLSRUSA-N (2r)-6-phenyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)hexanoic acid Chemical compound C([C@H](C(=O)O)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CCCC1=CC=CC=C1 MLBBPXVRDNIHJC-OAQYLSRUSA-N 0.000 claims description 2
NFBUUTBIBAVKLD-JOCHJYFZSA-N (2r)-7-phenyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)heptanoic acid Chemical compound C([C@H](C(=O)O)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CCCCC1=CC=CC=C1 NFBUUTBIBAVKLD-JOCHJYFZSA-N 0.000 claims description 2
SFBFEJANKUXLMO-OAQYLSRUSA-N (2r)-n-hydroxy-4-(1h-indol-3-yl)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanamide Chemical compound C1CCCC(OC2=C3)=C1C2=CC=C3S(=O)(=O)N[C@@H](C(=O)NO)CCC1=CNC2=CC=CC=C12 SFBFEJANKUXLMO-OAQYLSRUSA-N 0.000 claims description 2
MSIJLLVHAOLDGD-LJQANCHMSA-N (2r)-n-hydroxy-4-(phenylsulfamoyl)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanamide Chemical compound C([C@H](C(=O)NO)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CS(=O)(=O)NC1=CC=CC=C1 MSIJLLVHAOLDGD-LJQANCHMSA-N 0.000 claims description 2
YIAJDZLMFYJENV-LJQANCHMSA-N (2r)-n-hydroxy-4-phenyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanamide Chemical compound C([C@H](C(=O)NO)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CC1=CC=CC=C1 YIAJDZLMFYJENV-LJQANCHMSA-N 0.000 claims description 2
FKKVCOCMAOHGMH-JOCHJYFZSA-N (2r)-n-hydroxy-7-phenyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)heptanamide Chemical compound C([C@H](C(=O)NO)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CCCCC1=CC=CC=C1 FKKVCOCMAOHGMH-JOCHJYFZSA-N 0.000 claims description 2
ANWFOUUTHJPKJL-RUZDIDTESA-N (2r)-n-hydroxy-8-(1h-indol-3-yl)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)octanamide Chemical compound C1CCCC(OC2=C3)=C1C2=CC=C3S(=O)(=O)N[C@@H](C(=O)NO)CCCCCCC1=CNC2=CC=CC=C12 ANWFOUUTHJPKJL-RUZDIDTESA-N 0.000 claims description 2
POSNPMBRLUAHBF-HSZRJFAPSA-N (2r)-n-hydroxy-8-phenyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)octanamide Chemical compound C([C@H](C(=O)NO)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CCCCCC1=CC=CC=C1 POSNPMBRLUAHBF-HSZRJFAPSA-N 0.000 claims description 2
WWVQYHKZZQWIJX-HNNXBMFYSA-N (2s)-2-(2,3-dihydro-1h-cyclopenta[b][1]benzofuran-6-ylsulfonylamino)-3-methylbutanoic acid Chemical compound O1C2=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C2C2=C1CCC2 WWVQYHKZZQWIJX-HNNXBMFYSA-N 0.000 claims description 2
PIACOSNINDXKNU-LBPRGKRZSA-N (2s)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanedioic acid Chemical compound C1CCCC2=C1C1=CC=C(S(=O)(=O)N[C@@H](CC(=O)O)C(O)=O)C=C1O2 PIACOSNINDXKNU-LBPRGKRZSA-N 0.000 claims description 2
MNTISXAWZZNIAP-FQEVSTJZSA-N (2s)-3-(1h-indol-3-yl)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)propanoic acid Chemical compound C1CCCC(OC2=C3)=C1C2=CC=C3S(=O)(=O)N[C@H](C(=O)O)CC1=CNC2=CC=CC=C12 MNTISXAWZZNIAP-FQEVSTJZSA-N 0.000 claims description 2
RQOMZODPDMUHQB-KRWDZBQOSA-N (2s)-3-methyl-2-(6,7,8,9-tetrahydro-5h-fluoren-2-ylsulfonylamino)butanoic acid Chemical compound C1CCCC2=C1CC1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C12 RQOMZODPDMUHQB-KRWDZBQOSA-N 0.000 claims description 2
CAARDUCPOPELJI-INIZCTEOSA-N (2s)-3-methyl-2-(6,7,8,9-tetrahydrodibenzothiophen-3-ylsulfonylamino)butanoic acid Chemical compound C1CCCC2=C1C1=CC=C(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)C=C1S2 CAARDUCPOPELJI-INIZCTEOSA-N 0.000 claims description 2
CAEWMNQQSJLRTO-NRFANRHFSA-N (2s)-4-(1h-indol-3-yl)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanoic acid Chemical compound C1CCCC(OC2=C3)=C1C2=CC=C3S(=O)(=O)N[C@H](C(=O)O)CCC1=CNC2=CC=CC=C12 CAEWMNQQSJLRTO-NRFANRHFSA-N 0.000 claims description 2
IDZXKDMOCMXAPR-FQEVSTJZSA-N (2s)-4-benzylsulfanyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CSCC1=CC=CC=C1 IDZXKDMOCMXAPR-FQEVSTJZSA-N 0.000 claims description 2
WQTGBJAPYVORGF-FQEVSTJZSA-N (2s)-4-benzylsulfanyl-n-hydroxy-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanamide Chemical compound C([C@@H](C(=O)NO)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CSCC1=CC=CC=C1 WQTGBJAPYVORGF-FQEVSTJZSA-N 0.000 claims description 2
JQKACVYQFTUZRS-QFIPXVFZSA-N (2s)-4-phenyl-2-(6,7,8,9-tetrahydro-5h-fluoren-2-ylsulfonylamino)butanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=C2CC3=C(CCCC3)C2=CC=1)CC1=CC=CC=C1 JQKACVYQFTUZRS-QFIPXVFZSA-N 0.000 claims description 2
XQQJAHROIBOIEN-IBGZPJMESA-N (2s)-4-phenyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CC1=CC=CC=C1 XQQJAHROIBOIEN-IBGZPJMESA-N 0.000 claims description 2
NFBUUTBIBAVKLD-QFIPXVFZSA-N (2s)-7-phenyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)heptanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CCCCC1=CC=CC=C1 NFBUUTBIBAVKLD-QFIPXVFZSA-N 0.000 claims description 2
XJQNTOUGNJLTEI-QHCPKHFHSA-N (2s)-8-phenyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)octanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CCCCCC1=CC=CC=C1 XJQNTOUGNJLTEI-QHCPKHFHSA-N 0.000 claims description 2
AFKSZKIAONISER-HNNXBMFYSA-N (2s)-n-hydroxy-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)-3-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)propanamide Chemical compound O=C1C(C)(C)N(C)C(=O)N1C[C@@H](C(=O)NO)NS(=O)(=O)C1=CC=C(C2=C(CCCC2)O2)C2=C1 AFKSZKIAONISER-HNNXBMFYSA-N 0.000 claims description 2
DMHKCYMLAUKROF-FQEVSTJZSA-N (2s)-n-hydroxy-3-(1h-indol-3-yl)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)propanamide Chemical compound C1CCCC(OC2=C3)=C1C2=CC=C3S(=O)(=O)N[C@H](C(=O)NO)CC1=CNC2=CC=CC=C12 DMHKCYMLAUKROF-FQEVSTJZSA-N 0.000 claims description 2
PYUURZUOCYVISI-KRWDZBQOSA-N (2s)-n-hydroxy-3-methyl-2-[(9-methyl-5,6,7,8-tetrahydrocarbazol-2-yl)sulfonylamino]butanamide Chemical compound C1CCCC2=C1C1=CC=C(S(=O)(=O)N[C@@H](C(C)C)C(=O)NO)C=C1N2C PYUURZUOCYVISI-KRWDZBQOSA-N 0.000 claims description 2
MSIJLLVHAOLDGD-IBGZPJMESA-N (2s)-n-hydroxy-4-(phenylsulfamoyl)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanamide Chemical compound C([C@@H](C(=O)NO)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CS(=O)(=O)NC1=CC=CC=C1 MSIJLLVHAOLDGD-IBGZPJMESA-N 0.000 claims description 2
FNDCPICMMNEQGO-IBGZPJMESA-N (2s)-n-hydroxy-4-phenyl-2-(6,7,8,9-tetrahydrodibenzothiophen-3-ylsulfonylamino)butanamide Chemical compound C([C@@H](C(=O)NO)NS(=O)(=O)C=1C=C2SC=3CCCCC=3C2=CC=1)CC1=CC=CC=C1 FNDCPICMMNEQGO-IBGZPJMESA-N 0.000 claims description 2
QAWXUQHRVLWYIQ-NRFANRHFSA-N (2s)-n-hydroxy-6-phenyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)hexanamide Chemical compound C([C@@H](C(=O)NO)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CCCC1=CC=CC=C1 QAWXUQHRVLWYIQ-NRFANRHFSA-N 0.000 claims description 2
LIEAODBVUPRLNA-DEOSSOPVSA-N (2s)-n-hydroxy-7-(1h-indol-3-yl)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)heptanamide Chemical compound C1CCCC(OC2=C3)=C1C2=CC=C3S(=O)(=O)N[C@H](C(=O)NO)CCCCCC1=CNC2=CC=CC=C12 LIEAODBVUPRLNA-DEOSSOPVSA-N 0.000 claims description 2
FKKVCOCMAOHGMH-QFIPXVFZSA-N (2s)-n-hydroxy-7-phenyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)heptanamide Chemical compound C([C@@H](C(=O)NO)NS(=O)(=O)C=1C=C2OC=3CCCCC=3C2=CC=1)CCCCC1=CC=CC=C1 FKKVCOCMAOHGMH-QFIPXVFZSA-N 0.000 claims description 2
ANWFOUUTHJPKJL-VWLOTQADSA-N (2s)-n-hydroxy-8-(1h-indol-3-yl)-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)octanamide Chemical compound C1CCCC(OC2=C3)=C1C2=CC=C3S(=O)(=O)N[C@H](C(=O)NO)CCCCCCC1=CNC2=CC=CC=C12 ANWFOUUTHJPKJL-VWLOTQADSA-N 0.000 claims description 2
NPIPKUYPQOIUDY-LBPRGKRZSA-N (3s)-4-(hydroxyamino)-4-oxo-3-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfonylamino)butanoic acid Chemical compound C1CCCC2=C1C1=CC=C(S(=O)(=O)N[C@@H](CC(O)=O)C(=O)NO)C=C1O2 NPIPKUYPQOIUDY-LBPRGKRZSA-N 0.000 claims description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 4
150000002431 hydrogen Chemical group 0.000 claims 3
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 2
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Classifications

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- C07—ORGANIC CHEMISTRY
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07—ORGANIC CHEMISTRY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07—ORGANIC CHEMISTRY
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OA1200100027A 1998-07-30 1999-06-02 Tricyclic sulfonamides and their derivatives as inhibitors of matrix metalloproteinases. OA11589A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US9500698P	1998-07-30	1998-07-30

Publications (1)

Publication Number	Publication Date
OA11589A true OA11589A (en)	2004-07-30

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ID=22248526

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Application Number	Title	Priority Date	Filing Date
OA1200100027A OA11589A (en)	1998-07-30	1999-06-02	Tricyclic sulfonamides and their derivatives as inhibitors of matrix metalloproteinases.

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US (2)	US6420408B1 (id)
EP (1)	EP1100792B1 (id)
JP (1)	JP2002521478A (id)
KR (1)	KR20010072089A (id)
CN (1)	CN1310716A (id)
AP (1)	AP2001002037A0 (id)
AT (1)	ATE261954T1 (id)
AU (1)	AU758619B2 (id)
BG (1)	BG105185A (id)
BR (1)	BR9912600A (id)
CA (1)	CA2335077A1 (id)
DE (1)	DE69915634T2 (id)
DK (1)	DK1100792T3 (id)
EA (1)	EA200100158A1 (id)
EE (1)	EE200100063A (id)
ES (1)	ES2216614T3 (id)
GE (1)	GEP20033052B (id)
HR (1)	HRP20010078A2 (id)
HU (1)	HUP0102714A3 (id)
ID (1)	ID27192A (id)
IL (1)	IL140746A0 (id)
IS (1)	IS5810A (id)
NO (1)	NO20010479D0 (id)
NZ (1)	NZ509439A (id)
OA (1)	OA11589A (id)
PL (1)	PL345776A1 (id)
PT (1)	PT1100792E (id)
SK (1)	SK1192001A3 (id)
TR (1)	TR200100239T2 (id)
WO (1)	WO2000006561A1 (id)
YU (1)	YU6701A (id)
ZA (1)	ZA200100455B (id)

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MXPA01013171A (es) *	2001-02-14	2004-05-21	Warner Lambert Co	Inhibidores triciclicos de sulfonamida de metaloproteinasa de matriz.
CN1304390C (zh) *	2001-08-03	2007-03-14	先灵公司	新颖的γ—分泌酶抑制剂
US20040235957A1 (en) *	2001-10-12	2004-11-25	David Bleakman	Use of sulfonamide derivatives as pharmaceuticals compounds
ES2325205T3 (es) *	2001-12-20	2009-08-28	Bristol-Myers Squibb Company	Derivados de alfa-(n-sulfonamido)acetamida como inhibidores beta-amiloides.
PE20030701A1 (es)	2001-12-20	2003-08-21	Schering Corp	Compuestos para el tratamiento de trastornos inflamatorios
KR20050010882A (ko) *	2002-06-11	2005-01-28	와이어쓰	베타 아밀로이드 생산의 치환 페닐술폰아미드 저해제
MXPA05000754A (es) *	2002-07-17	2005-04-19	Warner Lambert Co	Combinacion de un inhibidor carboxilico alosterico de la metaloproteinasa de matriz-13 con celecoxib o valdecoxib.
US20050095267A1 (en) *	2002-12-04	2005-05-05	Todd Campbell	Nanoparticle-based controlled release polymer coatings for medical implants
US20040225077A1 (en)	2002-12-30	2004-11-11	Angiotech International Ag	Drug delivery from rapid gelling polymer composition
EP1613269B1 (en)	2003-04-04	2015-02-25	Incyte Corporation	Compositions, methods and kits relating to her-2 cleavage
ES2369498T3 (es)	2003-04-04	2011-12-01	Yeda Research And Development Co., Ltd.	Anticuerpos para inhibir la actividad de mmp-2 y mmp-9.
WO2005061448A1 (en) *	2003-12-24	2005-07-07	Monash University	Compositions and methods for treating vascular conditions
US20060112494A1 (en) *	2004-12-01	2006-06-01	David Oppong	Method of protecting an animal skin product from metalloproteinase activity
CN101702906B (zh) *	2007-02-23	2014-02-12	耶达研究及发展有限公司	用于抑制金属蛋白活性的抗体和含有所述抗体的药物组合物
US8012947B2 (en) *	2007-03-15	2011-09-06	Hospital For Special Surgery	Methods and compositions for promoting wound healing
US20090285840A1 (en) *	2008-04-29	2009-11-19	New York Society For The Ruptured And Crippled Maintaining The Hospital For Special Surgery	Methods for treating pathological neovascularization
CA2676946A1 (en)	2009-08-28	2011-02-28	Lucie Peduto	Adam12 inhibitors and their use against inflammation-induced fibrosis
EP2619179A1 (en)	2010-09-24	2013-07-31	Ranbaxy Laboratories Limited	Matrix metalloproteinase inhibitors
WO2017134265A1 (en)	2016-02-05	2017-08-10	Institut Pasteur	Use of inhibitors of adam12 as adjuvants in tumor therapies
WO2021147882A1 (zh) *	2020-01-21	2021-07-29	深圳信立泰药业股份有限公司	一种二苯并呋喃类衍生物组织蛋白酶k抑制剂及其制备方法和医药用途

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CH542837A (de) *	1970-03-20	1973-10-15	Ciba Geigy Ag	Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren, ihren Salzen und funktionellen Derivaten
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US5883940A (en)	1996-07-01	1999-03-16	Teledynamics Group, Inc.	Interactive method and apparatus for the generation of leads
ATE282602T1 (de)	1996-08-16	2004-12-15	Warner Lambert Co	Buttersäure matrix-metalloproteinase-inhibitoren
CA2256631A1 (en) *	1996-09-04	1998-03-12	Warner-Lambert Company	Compounds for and a method of inhibiting matrix metalloproteinases
KR20000068414A (ko) *	1996-09-04	2000-11-25	로즈 암스트롱, 크리스틴 에이. 트러트웨인	매트릭스 메탈로프로테이나제 억제제 및 그의 치료적 용도
HUP0000641A3 (en) *	1996-10-16	2001-02-28	American Cyanamid Company Madi	Ortho-sulfonamido aryl hydroxamic acid derivatives, their use, as matrix metalloproteinase and tace inhibitors and pharmaceutical compositions containing them

1999
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- 1999-06-02 DK DK99963141T patent/DK1100792T3/da active
- 1999-06-02 JP JP2000562364A patent/JP2002521478A/ja active Pending
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- 1999-06-02 ES ES99963141T patent/ES2216614T3/es not_active Expired - Lifetime
- 1999-06-02 PT PT99963141T patent/PT1100792E/pt unknown
- 1999-06-02 AT AT99963141T patent/ATE261954T1/de not_active IP Right Cessation
- 1999-06-02 GE GEAP19995773A patent/GEP20033052B/en unknown
- 1999-06-02 HU HU0102714A patent/HUP0102714A3/hu unknown
- 1999-06-02 AP APAP/P/2001/002037A patent/AP2001002037A0/en unknown
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- 1999-06-02 ID IDW20010198A patent/ID27192A/id unknown
- 1999-06-02 KR KR1020017001206A patent/KR20010072089A/ko not_active Withdrawn
- 1999-06-02 PL PL99345776A patent/PL345776A1/xx not_active Application Discontinuation
- 1999-06-02 TR TR2001/00239T patent/TR200100239T2/xx unknown
- 1999-06-02 HR HR20010078A patent/HRP20010078A2/hr not_active Application Discontinuation
- 1999-06-02 EE EEP200100063A patent/EE200100063A/xx unknown
- 1999-06-02 DE DE69915634T patent/DE69915634T2/de not_active Expired - Fee Related
- 1999-06-02 CN CN99808838A patent/CN1310716A/zh active Pending
- 1999-06-02 OA OA1200100027A patent/OA11589A/en unknown
- 1999-06-02 AU AU43292/99A patent/AU758619B2/en not_active Ceased
- 1999-06-02 WO PCT/US1999/012273 patent/WO2000006561A1/en not_active Ceased
- 1999-06-02 CA CA002335077A patent/CA2335077A1/en not_active Abandoned
- 1999-06-02 EA EA200100158A patent/EA200100158A1/ru unknown
2001
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- 2001-01-16 ZA ZA200100455A patent/ZA200100455B/en unknown
- 2001-01-25 BG BG105185A patent/BG105185A/xx unknown
- 2001-01-29 NO NO20010479A patent/NO20010479D0/no not_active Application Discontinuation
- 2001-04-10 US US09/719,027 patent/US6420408B1/en not_active Expired - Fee Related
2002
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Also Published As

Publication number	Publication date
US20020169164A1 (en)	2002-11-14
DE69915634T2 (de)	2004-08-12
ATE261954T1 (de)	2004-04-15
BG105185A (en)	2002-04-30
EE200100063A (et)	2002-06-17
IS5810A (is)	2001-01-12
US6492422B2 (en)	2002-12-10
BR9912600A (pt)	2001-05-02
DK1100792T3 (da)	2004-07-05
US6420408B1 (en)	2002-07-16
DE69915634D1 (de)	2004-04-22
TR200100239T2 (tr)	2001-05-21
CA2335077A1 (en)	2000-02-10
NO20010479L (no)	2001-01-29
EA200100158A1 (ru)	2001-08-27
EP1100792A1 (en)	2001-05-23
ID27192A (id)	2001-03-08
ZA200100455B (en)	2002-01-16
AP2001002037A0 (en)	2001-03-31
CN1310716A (zh)	2001-08-29
AU4329299A (en)	2000-02-21
NO20010479D0 (no)	2001-01-29
AU758619B2 (en)	2003-03-27
NZ509439A (en)	2002-10-25
HUP0102714A3 (en)	2003-01-28
PL345776A1 (en)	2002-01-02
KR20010072089A (ko)	2001-07-31
ES2216614T3 (es)	2004-10-16
GEP20033052B (en)	2003-08-25
JP2002521478A (ja)	2002-07-16
PT1100792E (pt)	2004-08-31
SK1192001A3 (en)	2002-02-05
WO2000006561A1 (en)	2000-02-10
EP1100792B1 (en)	2004-03-17
IL140746A0 (en)	2002-02-10
HRP20010078A2 (en)	2002-02-28
YU6701A (sh)	2003-12-31
HUP0102714A2 (hu)	2002-01-28

Publication	Publication Date	Title
US6420408B1 (en)	2002-07-16	Tricyclic sulfonamides and their derivatives as inhibitors of matrix metalloproteinases
US6350885B1 (en)	2002-02-26	Tricyclic heteroaromatics and their derivatives as inhibitors of matrix metalloproteinases
US6399612B1 (en)	2002-06-04	Heteroaryl butyric acids and their derivatives as inhibitors of matrix metalloproteinases
EP0876343B1 (en)	2002-03-13	Aromatic keto-acids and their derivatives as inhibitors of matrix metalloproteinases
US6117869A (en)	2000-09-12	Compounds for and methods of inhibiting matrix metalloproteinases
US6624196B2 (en)	2003-09-23	Benzene butyric acids and their derivatives as inhibitors of matrix metalloproteinases
US6265432B1 (en)	2001-07-24	Flourine-substituted biphenyl butyric acids and their derivatives as inhibitors of matrix metalloproteinases
US6677355B1 (en)	2004-01-13	Hydroxamic acid compounds useful as matrix metalloproteinase inhibitors
US6037361A (en)	2000-03-14	Fluorinated butyric acids and their derivatives as inhibitors of matrix metalloproteinases
MXPA00012948A (en)	2001-09-07	Tricyclic sulfonamides and their derivatives as inhibitors of matrix metalloproteinases
CZ2001302A3 (cs)	2001-07-11	Tricyklické sulfonamidy a jejich deriváty jako inhibitory matricových metaloproteináz
CA2233560C (en)	2005-12-20	Sulfonamide inhibitors of matrix metalloproteinases
MXPA98003315A (en)	1998-11-16	Queto aromatic acids and their derivatives as inhibitors of metaloproteinases mat
CA2236096A1 (en)	1997-07-03	Aromatic keto-acids and their derivatives as inhibitors of matrix metalloproteinases